Best Lewis Structure
The Lewis structure that is closest to your structure is determined.
The hybridization of the atoms in this idealized Lewis structure
is given in the table below.
Please note that your structure can't be well described by a single
Lewis structure, because of extensive delocalization.
Hybridization in the Best Lewis Structure
1. A bonding orbital for O1-C2 with 1.9903 electrons
__has 68.26% O 1 character in a sp2.60 hybrid
__has 31.74% C 2 character in a s0.80 p3 hybrid
2. A bonding orbital for O1-C9 with 1.9919 electrons
__has 67.57% O 1 character in a sp2.16 hybrid
__has 32.43% C 9 character in a sp2.77 hybrid
3. A bonding orbital for C2-C3 with 1.9937 electrons
__has 50.88% C 2 character in a sp2.28 hybrid
__has 49.12% C 3 character in a sp2.55 hybrid
4. A bonding orbital for C2-H7 with 1.9895 electrons
__has 57.80% C 2 character in a s0.96 p3 hybrid
__has 42.20% H 7 character in a s orbital
5. A bonding orbital for C2-H8 with 1.9895 electrons
__has 57.81% C 2 character in a s0.96 p3 hybrid
__has 42.19% H 8 character in a s orbital
6. A bonding orbital for C3-H4 with 1.9883 electrons
__has 59.11% C 3 character in a s0.92 p3 hybrid
__has 40.89% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 1.9912 electrons
__has 59.73% C 3 character in a s0.95 p3 hybrid
__has 40.27% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 1.9912 electrons
__has 59.73% C 3 character in a s0.95 p3 hybrid
__has 40.27% H 6 character in a s orbital
9. A bonding orbital for C9-C10 with 1.9947 electrons
__has 45.44% C 9 character in a p3 hybrid
__has 54.56% C10 character in a p3 hybrid
10. A bonding orbital for C9-C10 with 1.9923 electrons
__has 51.11% C 9 character in a sp1.31 hybrid
__has 48.89% C10 character in a sp1.59 hybrid
11. A bonding orbital for C9-H13 with 1.9845 electrons
__has 58.25% C 9 character in a sp2.26 hybrid
__has 41.75% H13 character in a s orbital
12. A bonding orbital for C10-H11 with 1.9863 electrons
__has 59.90% C10 character in a sp2.22 hybrid
__has 40.10% H11 character in a s orbital
13. A bonding orbital for C10-H12 with 1.9847 electrons
__has 59.49% C10 character in a sp2.27 hybrid
__has 40.51% H12 character in a s orbital
19. A lone pair orbital for O1 with 1.9735 electrons
__made from a sp1.44 hybrid
20. A lone pair orbital for O1 with 1.8981 electrons
__made from a p-pi orbital ( 99.96% p)
-With core pairs on: O 1 C 2 C 3 C 9 C10 -
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Donor Acceptor Interactions in the Best Lewis Structure
The localized orbitals in your best Lewis structure
can interact strongly. A filled bonding or lone pair orbital can
act as a donor and an empty or filled bonding, antibonding, or
lone pair orbital can act as an acceptor. These
interactions can strengthen and weaken bonds. For example, a
lone pair donor->antibonding acceptor orbital interaction
will weaken the bond
associated with the antibonding orbital. Conversly, an interaction
with a bonding pair as the acceptor will strengthen the bond.
Strong electron delocalization in your best Lewis structure will
also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair
orbitals are listed below.
The interaction of bonding donor orbital, 12, for C10-H11 with
the antibonding acceptor orbital, 166, for C9-H13 is 26.0 kJ/mol.
The interaction of bonding donor orbital, 13, for C10-H12 with
the antibonding acceptor orbital, 157, for O1-C9 is 34.3 kJ/mol.
The interaction of lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 166, for C9-H13 is 28.4 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O1 with
the antibonding acceptor orbital, 159, for C2-H7 is 29.7 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O1 with
the antibonding acceptor orbital, 160, for C2-H8 is 29.7 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O1 with
the antibonding acceptor orbital, 164, for C9-C10 is 153. kJ/mol.
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Molecular Orbital Energies
The orbital energies are given in eV, where 1 eV=96.49 kJ/mol.
Orbitals with very low energy are core 1s orbitals.
More antibonding orbitals than you might expect are sometimes
listed, because d orbitals are always included for heavy
atoms and p orbitals are included for H atoms.
Up spins are shown with a ^ and down spins are shown as v.
24 ----- 1.752
23 ----- 1.447
22 ----- 1.110
21 ----- -0.602
20 -^-v- -5.374
19 -^-v- -7.992
18 -^-v- -8.017
17 -^-v- -9.127
16 -^-v- -9.391
15 -^-v- -9.403
14 -^-v- -9.804
13 -^-v- -11.10
12 -^-v- -11.80
11 -^-v- -12.64
10 -^-v- -14.16
9 -^-v- -15.34
8 -^-v- -17.82
7 -^-v- -19.33
6 -^-v- -26.20
5 -^-v- -265.7
4 -^-v- -266.2
3 -^-v- -267.6
2 -^-v- -267.9
1 -^-v- -507.2
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Total Electronic Energy
The total electronic energy is a very large number, so by convention
the units are given in atomic units, that is Hartrees (H). One
Hartree is 2625.5 kJ/mol. The energy reference is for totally
dissociated atoms. In other words, the reference state is a gas
consisting of nuclei and electrons all at infinite distance from
each other. The electronic energy includes all electric
interactions and the kinetic energy of the electrons. This energy
does not include translation, rotation, or vibration of the
the molecule.
Total electronic energy = -232.5073488894 Hartrees
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